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For DS1 we stopped using the stroller around 3.5, mostly because he outgrew it. He could also walk pretty far at that age. We would still bring it with us if we were at the zoo or some kind of all day outing, but he rarely used it.

DS2 is 2.5 and already we rarely use the stroller! Only on all day outings and even then he usually only naps in it. We use it to hold all our stuff!

How much does he use it now? My oldest liked the stroller for a long time (past 4 for sure), but she’s less active overall. My middle is 4 and would ride in it some if I let him, but wouldn’t stay seated (and I want him to burn the energy because he’s a crazy man). They are 3 years apart and I got a sit and stand for #2’s arrival - it was only about $100 and came in handy anywhere we would walk a lot. But my 2nd and 3rd are 3.5 years apart and I’ve only used it once or twice in a year for them because 2nd is just not a stroller lover.

We haven’t used it yet but we got a Joovy Caboose S to use with the baby and 3 year old. We don’t use a stroller much with the 3 year old anymore other than outings to the zoo/other places with a lot of walking.

The Joovy Caboose S can be a single or double stroller (with the add-on seat) and both seats have a weight limit of 55 lbs. My daughter is big too so she surpassed the limits for a lot of other strollers! Without add-on seat there’s a bench that the 3 year old can sit or stand on.

DS1 was almost 4 when DS2 came along and we got a used joovy caboose double. It was a good option for them both going on short walks/to and from school or park but I found it heavy to do with both of them for longer walks. 10 months later, DS1 now uses his bike or walks, only occasionally we use the double stroller. We tend to use our city mini single just for DS2 now and we did buy a used double chariot for running too if needed (haven’t used much) I would do a double but definitely buy used as I bet you won’t use it for too long. My older was definitely a stroller fan so I thought he would want it forever but he’s really matured this spring/summer wanting to bike or walk more.

We also have a wagon but even at 10 months old I don’t think our youngest is stable enough to stay put...and he’s been walking for a month now and very active/strong.

@Sams Mom: We could use an infant seat with bird but it was awkward and bulky, so it wasn’t super useful until she could sit up on her own. In our case it really wasn’t until our oldest was almost four that we actually could use it much, as the baby couldn’t sit up until the middle of winter.

Our baby was born in October and our oldest turned 4 shortly after that. We live in the city and we bought a used bike trailer that doubles as a stroller and converts to a jogging stroller. I don’t know the weight limit but our kiddo is 45” and still fits in it easily. We used it a TON in the wintertime and it’s great bc it has a built in wind/rain screen. I go to stroller Strides with both kids most weekends, so we use it there. My daughter gets jealous of the baby and whines endlessly about having to walk if her sister is riding in the stroller. We actually ended up getting a rider board to attach to our BOB as well, which is nice because it clips up out of the way when she isn’t using it. It is a bit obnoxious to push the stroller with but has been so great for amusement parks, etc.

I know a lot of people whose 5 and 6 year olds still ride in their Bobs. You could also look at something like the Keenz stroller wagon, which one of our friends got and their 4 and 1 year olds love it.

We use it on long trips, like going to disneyland or to other amusement parks... we have this one and it holds 50lbs per seat

https://www.zoestrollers.com/p/zoe-xl2

@Ms.Mermaid: we did the same thing with the bike trailer/stroller and while it was nice to have the option, we didn’t use it much because by the time baby #2 could ride in it (~1) my then five year old was biking or scooting most of the time.
@Sams Mom: my kids are 3 years and 11 months apart and we never did a double stroller. I pushed my older in our single a few times with baby in a carrier, but he wasn’t a big baby wearing fan. I tried to get my daughter to walk/scooter/bike instead, but if she wasn’t in the mood I was out of luck. I did really miss being able to pop her in the stroller and go for long walks. In retrospect I feel like a double would have given me a lot more freedom for that first year and would have been worth it, I just couldn’t justify the cost at the time. It sounds like insurance is paying for it? If so I’d definitely go double! Even if you only use it for a year that is a long time in infant-needing-to-get-out-of-the-house-time!

@Sams Mom: My husband has only jogged with the kids once, but jogging strollers handle so well anyway that it's worth it to have a double jogger. The BOB pushes really easily/smoothly. The CityMini GT double has their nice easy fold, the pneumatic tires which I think you can use for light jogging (though they say you can't...) and doesn't take up a ton of space. Oooh, what about a Phil and Ted's that you can jog with? The only downside is you have no storage if you have both kids in it, I think, but you can always add a handlebar bag for small things or wear a backpack. That's probably your best jogging option to have a single/double option. But, I really like having our double stroller set up and a single stroller set up so I don't have to reconfigure it every time I'm trying to leave the house.

@CObee: We have the infant insert for our Chariot which we started using around 7-8 weeks.

Oh wow, I am surprised your 4 year old would even still use it. My 4-year old would laugh at me if I asked her to sit in a stroller But then again even my 2.5 year old twins are seldom in a stroller anymore.

So I would defintely be looking at single strollers - can your DS ride his (balance) bike or something when you're out? That's what my kids do a lot when we're out.

My 5.5 y/o still uses ours She’s almost outgrown our BOB Duallie which maxes out at 50lbs per kid (it tipped when I pushed it up a slant yesterday). Our playground is about a half mile away and going there and back after a long day at school is really too tough. Also if we didn’t have the double stroller we would have to drive much more often as we’re about a mile from the restaurants, stores, and farmers market in our town and it seems silly to drive that distance (except in winter!). We had a festival and 4th of July recently and walked 3.5 and 3 miles each time and brought all our swim stuff and party food in the stroller—definitely couldn’t do that with one kid walking. So I think it depends on the kid and your lifestyle, but I would get something like a Joovy Caboose. Oh and if grandparents will be watching them at all I’d say absolutely get a double.

Our boys are 4 years apart and we did not get a double stroller. Our oldest stopped using the stroller before 3. He rode a bike, used his scooter, or walked if I wanted to get out for a walk with baby. We don’t live in a walkable area aside from being able to walk to our local park.

I bought a cheapie double umbrella stroller for when we went to Disney when my kids were 11 mos and 4.5 and they both used it ..... DD is now 5.5 and weighs over 40 lbs but she will still use it if we are out for lots of walking.. For example we went to DC to go to a Smithsonian. Well with parking and walking to the museum and in the museum she sat in it the whole walk there and back and occasionally in the museum. So even though she exceeds the weight limit AND she's almost 6 and is capable of walking she will still sit in it when I have it. DS is the same but he's only 2. Needless to say I am happy I bought it and we have def gotten our money's worth. I think it was like $60 and we've had it now for 2 yrs and still use it.
https://www.amazon.com/gp/product/B003TRZIGW/ref=ppx_yo_dt_b_asin_title_o01_s00?ie=UTF8&th=1

My DD1 was 3.5 when bro was born but she loves walking so we did not get a double (even at Disney, she walked at 4). My 2nd was only two when his sister was born and even though I debated, we still did not get one. BUT...we don't walk a lot.

I would also baby wear baby and put #2 in stroller. We also bought this stroller handle that I taught #2 to hold so he's holding on to stroller and walking.

My kid is nearly 4 and uses the umbrella stroller and double bob all the time and always has, but I know a lot of kids don’t like the stroller after a certain age. I’m very glad I have a double though. I got it used. If you aren’t planning on doing lots of walking though and have parks close by then a good jogging type single stroller with a higher weight limit and a stroller board should be adequate for your kid(S). Then if you need to you can baby wear and put your older one in the stroller. So I’d just throw your carrier in the basket of the single just in case and hit the road!

My 4yo either stands on our Lascal Buggy Board or rides his scooter / bike and I carry him in our toddler Beco on occasion. My 6 and 4yo are both quite capable of walking / biking / scooting over a mile and we live up a big hill!

We have a Joovy Caboose Ultralight, and it is an absolute lifesaver for my almost 4-year old (he'll turn 4 in two weeks) and 2 year old. He can jump on and off easily for places like the zoo, but there's also a seat so he can sit down if he's feeling tired. https://www.amazon.com/Joovy-Caboose-Ultralight-Graphite-Stroller/dp/B01BMAW0T0/ref=sr_1_2_sspa?keywords=joovy%2Bcaboose%2Bultralight&qid=1562809593

@Littlebit7: just want to say, so jealous.

@gotkimchi: I’m not a parade person; I’ve lived in the nyc area for 10+ years and never been to a ticker tape parade. I have to say.,..it was pretty awesome. I had tears in my eyes a few times. My daughter is young, only 4, but I felt this moral obligation to SHOW her. It was a long day for her; we walked past the wtc memorial which is hard to explain to a 4 yo, but also something that had to be done. Anyway, all that to say, I’m glad we went. It was pretty special.